One-to-one questions, grouped by the situation you are in

Echipa HR 365 · reviewed 2026-09-02 · 5 min read

A good one-to-one has three or four questions and repeats them from one meeting to the next, because the value comes from comparison, not variety. What changes is the situation: the first one-to-one with a new person, a routine one, and one with somebody who seems demotivated call for different sets.

The basic rule: it is not your meeting

The most frequent failed form of one-to-one is the activity report: the person says what they did, the manager confirms, both leave feeling something was ticked off. Status can be sent in writing in three minutes. The meeting is for what does not get written: where they got stuck, what is unclear, what decision they are waiting on from you.

Set 1 — the first one-to-one with a new person

• What was least clear in your first week? (this catches the gaps in onboarding while they can still be fixed)
• Who has helped you most so far? (it shows you the real mentor, who is not always the assigned one)
• What do you need from me so that you do not get stuck?
• How do you prefer to receive feedback: on the spot or in a separate conversation?

The last question looks procedural and is the most useful in the long run: it tells you how to hold every difficult conversation from now on, and you learn it before you have one.

Set 2 — the routine one-to-one

• What has held you up since last time?
• What have you done that nobody noticed?
• What decision are you waiting on from me?
• What should I be doing differently?

The second question deserves an explanation. Most well-done work is invisible, and people do not claim it themselves, least of all the ones who work best. The question gives them permission and gives you material for the review — material you would otherwise never learn.

The fourth is the one that gets avoided. Asked consistently, at every meeting, it gets real answers only from the third or fourth time. Asked once, out of curiosity, it gets “nothing, everything is fine” and that is that.

Set 3 — when somebody seems demotivated

The bad question here is “is everything alright?”. It gets a “yes” in two seconds and closes the conversation. Ask about facts, not about feelings:

• What has changed in the last few weeks in what you work on?
• Of everything you do now, what would you hand to somebody else tomorrow, if you could?
• What annoyed you most this month?
• Which part of the work do you enjoy most — and how much of your time does it take?

The last pair is the most productive in this whole article. Usually the answer is that the favourite part takes 10% of the time and the rest has filled up with something else. That is a solvable problem, unlike “I have lost interest”, which is not.

Set 4 — the one-to-one before a review

• What do you think was your best piece of work this period?
• What would you do differently if you did it again?
• What would you like your role to do in a year that it does not do now?
• What would make you stay here another two years?

What you do not ask and what you do not do

• Nothing about private life, health or family, however friendly the relationship.
• Nothing about colleagues phrased as an assessment of them. “How is working with X going” is fine; “what do you think of X” is not.
• No question you are not prepared to answer or act on. Questions without follow-through teach people the meeting is a formality.
• Do not cancel. A one-to-one postponed three times running communicates more clearly than anything you could say at the fourth.

The last five minutes, which make the difference

1. Manager — summarises out loud what was decided, so you are sure you understood the same thing
2. Manager — writes down the two or three points somewhere the person can see them too, not just in their own notebook
3. Manager — starts the next meeting from them — otherwise the notes serve no purpose

What you record and where

Notes from a one-to-one have one rule that matters: the person sees them too. A manager’s private notebook produces, over time, a version of the conversation the other party does not know about — and at review time surprises appear that should never have existed.

• The decisions taken, phrased as actions with an owner and a deadline. Not “we will discuss X”, but “I will speak to Y by Friday”.
• What the person asked for and has not received yet. It is the list you check first next time and the only way not to lose legitimate requests.
• Observations for the review, written then rather than reconstructed six months later. Three lines a month means a review based on facts.

What does not get recorded: assessments of the person, passing moods, and anything about their private life, even if volunteered. A journal of that kind helps nobody and becomes a problem the day somebody asks to see it.

How often and how long?

Weekly or fortnightly, 30 minutes. Monthly is too rare to catch things while they are small; an hour weekly is hard to sustain and is the first thing cancelled.

What if the person has nothing to say?

It usually means they have not understood what the meeting is for, or that previous answers had no follow-through. Start with set 2, question three — “what decision are you waiting on from me” almost always produces something.